Pharmaceutical agents are a standard treatment for a variety of ailments. The low cost, ease of administration, and efficacy make drugs a near ideal form of prevention or treatment. Regretfully, most of these medications are derived from limited global supplies of petroleum. For this reason, more sustainable methods of manufacturing pharmaceuticals are needed. This proposal aims to develop a novel chemical reaction to synthesize substituted piperidine rings via the activation of otherwise inert C-H bonds. Piperidines are the focus of this work because of their frequency in FDA approved drugs including donepezil (Alzheimer's), benzatropine (Parkinson's), fentanyl (pain), and astemizole (allergies). Because they are common to nearly all organic molecules, the direct functionalization of C-H bonds is a rapid and efficient way to obtain the complex molecules needed to make pharmaceuticals. To activate C-H bonds, this proposal aims to utilize Pd catalysis via a PdII/PdIV catalytic cycle. This proposal avoids the use of superfluously added directing groups by taking direct advantage of the piperidine nitrogen's lone pair electrons. Completion of the proposed research should facilitate a more economical and sustainable method to synthesize piperidine containing pharmaceuticals. This proposal also aims to quantify the efficiency gains of this and other work using green manufacturing metrics. This quantification should provide a benchmark in progress towards making pharmaceutical synthesis sustainable.